A mountainous landscape with large boulders and distant hills.

Holiday Rentals in Madison County

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Our top choices for Madison County holiday rentals

A hallway with a wooden bench, a red door, and a framed picture on the wall.

1. Historic Madison Eagle Inn

Historic Madison Eagle Inn
Madison
10.0 out of 10, Exceptional, (19 reviews)
"Great place - clean and very easy parking. The bed was comfortable too!"
United States
Tracy
The price is €231
includes taxes & fees
2 Nov - 3 Nov
Historic Madison Eagle Inn
A modern kitchen with a central island, bar stools, and pendant lighting.

2. Barn Apartment on Farm Near Old Rag and Shenandoah National Park

Barn Apartment on Farm Near Old Rag and Shenandoah National Park
Etlan
10.0 out of 10, Exceptional, (34 reviews)
"Kids absolutely loved the property with many kinds of animals!"
United States
Ikuo
The price is €171
includes taxes & fees
28 Oct - 29 Oct
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
A cabin with a wooden deck, two chairs, a red door, and a window.

3. Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
Etlan
9.8 out of 10, Exceptional, (23 reviews)
"Hose was excellent, great communication, helpful, answered questions, even returned items inadvertently left behind. Location was great for activities around the national park and caverns."
United States
Tracy P.
The price is €104
includes taxes & fees
26 Oct - 27 Oct
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

4. Charming 4-bedroom house in Madison centrally located!

Charming 4-bedroom house in Madison centrally located!
Madison
10.0 out of 10, Exceptional, (4 reviews)
"The home met all our family’s needs during a weekend stay for a party at nearby farm. The layout and outdoor spaces were a bonus. In fact, the view of Hawksbill Mountain from the porch while enjoying our morning coffee: priceless. And importantly easy access to Rt 29 and the town but yet secluded and bucolic."
United States
B D.
The price is €401
includes taxes & fees
25 Oct - 26 Oct
Charming 4-bedroom house in Madison centrally located!
A covered deck with blue and turquoise Adirondack chairs, a white chair, and a green doormat.

5. The Cabin at the Lake

The Cabin at the Lake
Madison
9.6 out of 10, Exceptional, (66 reviews)
"Perfect little getaway."
United States
Vernon M.
The price is €268
includes taxes & fees
26 Oct - 27 Oct
The Cabin at the Lake
S'mores anyone?

6. Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse

Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
Sperryville
10.0 out of 10, Exceptional, (32 reviews)
"The property was great -- would definitely book again!"
United States
Everett R.
The price is €557
includes taxes & fees
17 Nov - 18 Nov
Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
A spacious kitchen with modern appliances, a dining area with a large table, and a cozy living area with a sofa and coffee table.

7. Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues

Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
Madison
8.0 out of 10, Very good, (1 review)
"Positive Highlights: quiet location still close to Skyline Drive, amenities, fresh interior recently modernized, love for details (charging cables, coffee bar, etc)"
United States
Birgit W.
The price is €430
includes taxes & fees
25 Oct - 26 Oct
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
A spacious living room with a high wooden ceiling, large windows, a sofa, armchairs, a coffee table, and a dining area.

8. Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres

Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
Etlan
9.4 out of 10, Exceptional, (73 reviews)
"Wonderful house and great setting; will go back!"
United States
Jay R.
The price is €668
includes taxes & fees
25 Oct - 26 Oct
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
A log cabin interior with a wooden ceiling, a black leather sofa, white armchairs, and a rustic dining area.

9. Walk to Old Rag | Hot Tub | Mountain Farmhouse

Walk to Old Rag | Hot Tub | Mountain Farmhouse
Sperryville
10.0 out of 10, Exceptional, (28 reviews)
"Wonderful house. Great location for hiking old rag."
United States
Jeffrey C.
The price is €584
includes taxes & fees
26 Oct - 27 Oct
Walk to Old Rag | Hot Tub | Mountain Farmhouse
Three artificial butterflies mounted on poles with a tree in the background.

10. Butterfly Camp near Old Rag Mountain and Shenandoah National Park

Butterfly Camp near Old Rag Mountain and Shenandoah National Park
Etlan
The price is €160
includes taxes & fees
25 Oct - 26 Oct
Butterfly Camp near Old Rag Mountain and Shenandoah National Park
A glass enclosure with a view of a forest interior, including a bed and various plants.

11. Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
2.5 star property
Stanardsville
9.4 out of 10, Exceptional, (148 reviews)
"Loved everything about my stay, customer service was amazing and I’m definitely making this an animal visit!"
United States
Promise
The price is €194
includes taxes & fees
22 Nov - 23 Nov
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
A two-story house with a stone facade, a front porch, and a well-maintained lawn.

12. Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+

Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
Stanardsville
10.0 out of 10, Exceptional, (33 reviews)
"Stayed here for a weekend while hiking Old Rag in Shenandoah. Cozy little place that was well equipped with all the amenities we needed! It's conveniently located close to Shenandoah as well as plenty of vineyards. Would not hesitate to stay here again the next time we're in the area!"
United States
Jason
The price is €202
includes taxes & fees
27 Oct - 28 Oct
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
A spacious living room with a large beige sectional sofa, two blue armchairs, a wooden coffee table, and a floor lamp.

13. Boardwalk Hotel on Lake Anna by Kasa

Boardwalk Hotel on Lake Anna by Kasa
4.0 star property
Louisa
9.0 out of 10, Wonderful, (149 reviews)
"A very nice place. Very clean and comfortable. Would definitely stay again."
United States
Stephanie
The price is €113
includes taxes & fees
8 Nov - 9 Nov
Boardwalk Hotel on Lake Anna by Kasa
A modern house with a deck, surrounded by a well-maintained lawn and trees.

14. Whispering Hillside -Coffee Bar, Hot Tub Fire Pit

Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
Stanley
9.2 out of 10, Wonderful, (62 reviews)
"Absolutely wonderful stay in every way!! Would definitely rent this house again!!! "
United States
Kim W.
The price is €321
includes taxes & fees
16 Nov - 17 Nov
Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
A wooden deck with Adirondack chairs and a table, surrounded by dense forest and a stream.

15. The House in the Holla at the foot of Shenandoah National Park

The House in the Holla at the foot of Shenandoah National Park
Stanardsville
9.8 out of 10, Exceptional, (99 reviews)
"Clean, sweet, and quiet. Perfect for a weekend away from everything "
United States
Piper G.
The price is €226
includes taxes & fees
27 Oct - 28 Oct
The House in the Holla at the foot of Shenandoah National Park
A forested area with a fire pit and Adirondack chairs.

16. Moonfire Farm Shenandoah region cozy getaway

Moonfire Farm Shenandoah region cozy getaway
Barboursville
9.8 out of 10, Exceptional, (42 reviews)
"It was a very pleasant stay. We chatted it up with Stuart the owner he was very nice. The place was super clean and we had everything we needed. We would totally stay again. Great experience!"
United States
Matt
The price is €192
includes taxes & fees
27 Oct - 28 Oct
Moonfire Farm Shenandoah region cozy getaway
Outdoor dining

17. 10 mins from Shenandoah National Park ~ Cozy Cabin

10 mins from Shenandoah National Park ~ Cozy Cabin
Elkton
10.0 out of 10, Exceptional, (15 reviews)
"We loved our stay there, it was only a night but the cottage has everything you need for a relaxing trip. The hot tub was super easy to use and the view of the woods was beautiful."
United States
Tamsin D.
The price is €326
includes taxes & fees
4 Nov - 5 Nov
10 mins from Shenandoah National Park ~ Cozy Cabin
A log cabin with a large window and a wooden door.

18. Beautiful Log Chalet, Hot Tub, Gas Grill, Secluded 6 wooded acres. Best privacy

Beautiful Log Chalet, Hot Tub, Gas Grill, Secluded 6 wooded acres. Best privacy
Stanley
8.4 out of 10, Very good, (86 reviews)
"It was a beautiful cabin, exactly what we needed to get away from the city and just disconnect. If you’re not comfortable driving on mountain roads, just something to think about. Overall an amazing little getaway. "
United States
Mike B.
The price is €367
includes taxes & fees
30 Oct - 31 Oct
Beautiful Log Chalet, Hot Tub, Gas Grill, Secluded 6 wooded acres. Best privacy
A grassy field with a wooden fence, trees, and a distant building.

19. Servants' Cottage on 600 Acre Working Horse/Cattle Estate

Servants' Cottage on 600 Acre Working Horse/Cattle Estate
Gordonsville
9.8 out of 10, Exceptional, (143 reviews)
"The cottage had everything you need."
United States
William J.
The price is €168
includes taxes & fees
26 Oct - 27 Oct
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
A round table with a grill in the center, surrounded by white Adirondack chairs, set on a wooden deck with a forest background.

20. NEW Colorful Cottage + Hot Tub + Pets + 15 min to LAKE

NEW Colorful Cottage + Hot Tub + Pets + 15 min to LAKE
Stanley
9.8 out of 10, Exceptional, (26 reviews)
"Very beautifully decorated, clean and well maintained cottage. We appreciate all detail info provided about the house and surroundings and especially the warm welcome with lights and hot tub ready to use. It's located in more secluded location but not too far from local attractions, so we enjoyed hiking in Shanendoah NP. Wisteria Winery 5 min from cottage is awesome too."
United States
Marta D.
NEW Colorful Cottage + Hot Tub + Pets + 15 min to LAKE
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Madison County Hotel Reviews

Skyland

Skyland

8/10 Good
"Food is still terrible."
John 1-night trip
Posted 10 hours ago
Skyland

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Holiday Homes in Madison County

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